Hyperconjugation is the source of helicity in perfluorinated n-alkanes

Rodrigo A. Cormanich; David O'Hagan; Michael Buehl

doi:10.1002/anie.201704112

Hyperconjugation is the source of helicity in perfluorinated n-alkanes

Rodrigo A. Cormanich, David O'Hagan, Michael Buehl^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Hyperconjugative, steric and electrostatic effects were evaluated as possible sources of the helicity in linear perfluorinated alkanes through analysis of natural bond orbitals and classical electrostatics. Contrary to previous rationalisations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilisation through σ_CC-> σ*_CFinteractions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes

Original language	English
Pages (from-to)	7867-7870
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	27
Early online date	31 May 2017
DOIs	https://doi.org/10.1002/anie.201704112
Publication status	Published - 21 Jun 2017

Keywords

Conformational analysis
Density-functional calculations
Fluorocarbons
Helical structures
Hyperconjugation

Access to Document

10.1002/anie.201704112

Buehl_2017_ACIE_Helicity_AAM
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/anie.201704112
Accepted author manuscript, 720 KB

Michael Buehl
- mb105st-andrews.acuk
- School of Chemistry - Professor
- EaSTCHEM
Person: Academic

Cite this

@article{ceab0f4abb97425d9b564f007e90a41a,

title = "Hyperconjugation is the source of helicity in perfluorinated n-alkanes",

abstract = "Hyperconjugative, steric and electrostatic effects were evaluated as possible sources of the helicity in linear perfluorinated alkanes through analysis of natural bond orbitals and classical electrostatics. Contrary to previous rationalisations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilisation through σCC-> σ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes",

keywords = "Conformational analysis, Density-functional calculations, Fluorocarbons, Helical structures, Hyperconjugation ",

author = "Cormanich, {Rodrigo A.} and David O'Hagan and Michael Buehl",

note = "The authors thank FAPESP and EaStCHEM funding agencies.",

year = "2017",

month = jun,

day = "21",

doi = "10.1002/anie.201704112",

language = "English",

volume = "56",

pages = "7867--7870",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "John Wiley & Sons, Ltd",

number = "27",

}

TY - JOUR

T1 - Hyperconjugation is the source of helicity in perfluorinated n-alkanes

AU - Cormanich, Rodrigo A.

AU - O'Hagan, David

AU - Buehl, Michael

N1 - The authors thank FAPESP and EaStCHEM funding agencies.

PY - 2017/6/21

Y1 - 2017/6/21

N2 - Hyperconjugative, steric and electrostatic effects were evaluated as possible sources of the helicity in linear perfluorinated alkanes through analysis of natural bond orbitals and classical electrostatics. Contrary to previous rationalisations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilisation through σCC-> σ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes

AB - Hyperconjugative, steric and electrostatic effects were evaluated as possible sources of the helicity in linear perfluorinated alkanes through analysis of natural bond orbitals and classical electrostatics. Contrary to previous rationalisations, which indicate dominating steric or electrostatic effects, this analysis indicates that hyperconjugative stabilisation through σCC-> σ*CF interactions are the underlying driving force for the origin of the observed helicity in perfluoroalkanes

KW - Conformational analysis

KW - Density-functional calculations

KW - Fluorocarbons

KW - Helical structures

KW - Hyperconjugation

U2 - 10.1002/anie.201704112

DO - 10.1002/anie.201704112

M3 - Article

SN - 1433-7851

VL - 56

SP - 7867

EP - 7870

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 27

ER -

Hyperconjugation is the source of helicity in perfluorinated n-alkanes

Abstract

Keywords

Access to Document

Fingerprint

Profiles

Michael Buehl

Cite this